Application of the Photo-Fries Reaction as a Key Step in the Preparation of Valuable Aryloxyethyl Selenocyanates

LUCENA VALENTIN; SZAJNMAN SERGIO; JUAN B. RODRIGUEZ; BONESI SERGIO M

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

WILEY-V C H VERLAG GMBH

Lugar: Weinheim; Año: 2024

1434-193X

A multi-step sequence leads to the preparation of a series of aryl selenocyanate WC-9 homologues which are interesting compounds with potential biological activity against Trypanosoma cruzi, the etiological agent of Chagas disease. The synthetic sequence involves the application of the photo-Fries rearrangement reaction as a key step for the preparation of a series of 2-hydroxyphenones bearing alkyl chains of different length and a phenyl group. These intermediates are obtained upon direct irradiation (254 nm) of 4-phenoxyphenyl esters in different solvents at room temperature. Then, reaction of the 2-hydroxyphenones with 2-(2-bromoethoxy)tetrahydro-2H-pyran followed by acid deprotection, tosylation (or mesylation) reaction and, finally, nucleophilic attack with potassium selenocyanate provides the target aryloxyethyl selenocyanate homologues in good yields